Organic reaction in water. Part 4.For Part 3, see: T. Tsukinoki, T. Kanda, G. B. Liu, H. Tsuzuki and M. Tashiro, Tetrahedron Lett., in press. For Part 2, see G.-B. Liu, L. Tsukinoki, T. Kanda, Y. Mitoma and M. Tashiro, Tetrahedron Lett., 1998, 39, 5991. New synthesis of vicinal diamines using zinc powder-promoted carbon–carbon bond formation

Abstract

Reductive coupling of aromatic imines is performed by the use of zinc powder and additives such as NH₄Cl and L-tyrosine in water without any organic solvents under mild conditions to give the corresponding vicinal diamines in good yields; cross-coupling of N-benzylideneaniline and benzaldehyde similarly proceeds in aqueous media to afford the corresponding 2-aminoalcohol.